4-[(E)-4-Bromo-benzyl-ideneamino]-3-methyl-1H-1,2,4-triazole-5(4H)-thione.

In the title mol-ecule, C(10)H(9)BrN(4)S, the dihedral angle between the triazole and benzene rings is 12.32 (19)°. An intra-molecular C-H⋯S hydrogen bond generates an S(6) ring motif. In the crystal packing, centrosymmetrically related mol-ecules are linked into a dimer by N-H⋯S hydrogen bonds, and the dimers are linked into a chain running along [11] by Br⋯N short contacts [3.187 (3) Å]. The crystal packing is further strengthened by π-π inter-actions involving the triazole ring [centroid-centroid distance = 3.322 (2) Å].

Related literature

For the pharmacological activity of triazole compounds, see: Bekircan et al. (2006 ▶); Brandt et al. (2007 ▶); Holla et al. (1996 ▶, 2002 ▶); Yale et al. (1966 ▶). For bond-length data, see: Allen et al. (1987 ▶). For graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C10H9BrN4S

M = 297.18

Triclinic,

a = 6.9239 (5) Å

b = 7.6072 (5) Å

c = 11.5982 (8) Å

α = 82.453 (5)°

β = 88.339 (5)°

γ = 68.204 (4)°

V = 562.18 (7) Å3

Z = 2

Mo Kα radiation

μ = 3.82 mm−1

T = 100.0 (1) K

0.32 × 0.31 × 0.12 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.265, T max = 0.629

13535 measured reflections

3252 independent reflections

2538 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.121

S = 1.09

3252 reflections

146 parameters

H-atom parameters constrained

Δρmax = 1.20 e Å−3

Δρmin = −1.50 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808021636/ci2629sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808021636/ci2629Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C10H9BrN4S	Z = 2
Mr = 297.18	F000 = 296
Triclinic, P1	Dx = 1.756 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 6.9239 (5) Å	Cell parameters from 5175 reflections
b = 7.6072 (5) Å	θ = 2.9–33.2º
c = 11.5982 (8) Å	µ = 3.82 mm−1
α = 82.453 (5)º	T = 100.0 (1) K
β = 88.339 (5)º	Plate, colourless
γ = 68.204 (4)º	0.32 × 0.31 × 0.12 mm
V = 562.18 (7) Å3

Bruker SMART APEXII CCD area-detector diffractometer	3252 independent reflections
Radiation source: fine-focus sealed tube	2538 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.059
T = 100.0(1) K	θmax = 30.0º
φ and ω scans	θmin = 1.8º
Absorption correction: multi-scan(SADABS; Bruker, 2005)	h = −9→9
Tmin = 0.265, Tmax = 0.629	k = −10→10
13535 measured reflections	l = −16→16

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046	H-atom parameters constrained
wR(F2) = 0.121	w = 1/[σ2(Fo2) + (0.0635P)2 + 0.1826P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max = 0.001
3252 reflections	Δρmax = 1.20 e Å−3
146 parameters	Δρmin = −1.50 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Br1	1.07281 (6)	0.01690 (5)	0.76969 (3)	0.02379 (13)
S1	0.13495 (15)	0.36883 (13)	0.17836 (8)	0.0247 (2)
N1	0.5353 (5)	0.4917 (4)	0.2620 (2)	0.0212 (6)
N2	0.4008 (5)	0.5702 (4)	0.1661 (2)	0.0201 (6)
N3	0.1919 (5)	0.6408 (4)	0.0225 (3)	0.0243 (6)
N4	0.3110 (5)	0.7506 (4)	−0.0027 (3)	0.0236 (6)
C1	0.8184 (6)	0.3339 (5)	0.4542 (3)	0.0237 (7)
H1A	0.8534	0.4121	0.3957	0.028*
C2	0.9486 (6)	0.2514 (5)	0.5516 (3)	0.0246 (7)
H2A	1.0698	0.2751	0.5590	0.029*
C3	0.8955 (6)	0.1335 (5)	0.6374 (3)	0.0214 (7)
C4	0.7153 (6)	0.0956 (5)	0.6288 (3)	0.0230 (7)
H4A	0.6830	0.0140	0.6862	0.028*
C5	0.5843 (6)	0.1829 (5)	0.5321 (3)	0.0224 (7)
H5A	0.4606	0.1626	0.5265	0.027*
C6	0.6348 (5)	0.2997 (5)	0.4439 (3)	0.0199 (7)
C7	0.4924 (5)	0.3838 (5)	0.3443 (3)	0.0199 (7)
H7A	0.3710	0.3592	0.3407	0.024*
C8	0.2417 (6)	0.5275 (5)	0.1234 (3)	0.0217 (7)
C9	0.4376 (6)	0.7049 (5)	0.0860 (3)	0.0211 (7)
C10	0.5990 (6)	0.7828 (5)	0.1022 (3)	0.0249 (7)
H10A	0.6335	0.8346	0.0280	0.037*
H10B	0.7209	0.6828	0.1377	0.037*
H10C	0.5478	0.8818	0.1514	0.037*
H1N3	0.1157	0.6542	−0.0384	0.030*

	U11	U22	U33	U12	U13	U23
Br1	0.0287 (2)	0.02116 (18)	0.01825 (18)	−0.00691 (14)	−0.00647 (13)	0.00315 (12)
S1	0.0301 (5)	0.0264 (4)	0.0191 (4)	−0.0150 (4)	−0.0050 (3)	0.0069 (3)
N1	0.0242 (15)	0.0186 (13)	0.0177 (14)	−0.0058 (12)	−0.0047 (11)	0.0029 (11)
N2	0.0251 (14)	0.0185 (13)	0.0154 (13)	−0.0085 (12)	−0.0020 (11)	0.0041 (10)
N3	0.0318 (16)	0.0226 (14)	0.0179 (14)	−0.0120 (13)	−0.0029 (12)	0.0058 (11)
N4	0.0259 (15)	0.0242 (15)	0.0203 (14)	−0.0109 (13)	0.0003 (12)	0.0040 (11)
C1	0.0278 (18)	0.0222 (16)	0.0194 (16)	−0.0094 (14)	0.0024 (14)	0.0028 (13)
C2	0.0227 (17)	0.0252 (17)	0.0243 (18)	−0.0076 (14)	−0.0052 (14)	−0.0009 (14)
C3	0.0253 (17)	0.0167 (15)	0.0164 (15)	−0.0024 (13)	−0.0035 (13)	0.0022 (12)
C4	0.0307 (19)	0.0178 (15)	0.0188 (16)	−0.0083 (14)	0.0018 (14)	0.0007 (12)
C5	0.0255 (17)	0.0198 (16)	0.0225 (17)	−0.0100 (14)	−0.0034 (14)	0.0002 (13)
C6	0.0237 (16)	0.0176 (15)	0.0173 (15)	−0.0074 (13)	−0.0001 (13)	0.0003 (12)
C7	0.0239 (16)	0.0191 (15)	0.0158 (15)	−0.0079 (13)	−0.0044 (13)	0.0009 (12)
C8	0.0229 (16)	0.0210 (16)	0.0182 (16)	−0.0057 (14)	−0.0004 (13)	0.0006 (12)
C9	0.0252 (17)	0.0181 (15)	0.0195 (16)	−0.0088 (14)	−0.0006 (13)	0.0013 (12)
C10	0.0285 (18)	0.0230 (17)	0.0228 (17)	−0.0116 (15)	−0.0006 (14)	0.0047 (13)

Br1—C3	1.895 (3)	C2—C3	1.386 (5)
S1—C8	1.686 (4)	C2—H2A	0.93
N1—C7	1.278 (4)	C3—C4	1.390 (5)
N1—N2	1.390 (4)	C4—C5	1.392 (5)
N2—C8	1.380 (5)	C4—H4A	0.93
N2—C9	1.381 (4)	C5—C6	1.390 (5)
N3—C8	1.331 (4)	C5—H5A	0.93
N3—N4	1.377 (4)	C6—C7	1.455 (4)
N3—H1N3	0.87	C7—H7A	0.93
N4—C9	1.296 (5)	C9—C10	1.473 (5)
C1—C2	1.391 (5)	C10—H10A	0.96
C1—C6	1.400 (5)	C10—H10B	0.96
C1—H1A	0.93	C10—H10C	0.96
C7—N1—N2	119.6 (3)	C6—C5—H5A	119.4
C8—N2—C9	108.5 (3)	C4—C5—H5A	119.4
C8—N2—N1	133.0 (3)	C5—C6—C1	119.2 (3)
C9—N2—N1	118.1 (3)	C5—C6—C7	118.3 (3)
C8—N3—N4	114.1 (3)	C1—C6—C7	122.5 (3)
C8—N3—H1N3	137.0	N1—C7—C6	119.6 (3)
N4—N3—H1N3	108.1	N1—C7—H7A	120.2
C9—N4—N3	104.3 (3)	C6—C7—H7A	120.2
C2—C1—C6	120.3 (3)	N3—C8—N2	102.7 (3)
C2—C1—H1A	119.8	N3—C8—S1	126.6 (3)
C6—C1—H1A	119.8	N2—C8—S1	130.6 (3)
C3—C2—C1	119.2 (4)	N4—C9—N2	110.4 (3)
C3—C2—H2A	120.4	N4—C9—C10	126.1 (3)
C1—C2—H2A	120.4	N2—C9—C10	123.5 (3)
C2—C3—C4	121.7 (3)	C9—C10—H10A	109.5
C2—C3—Br1	119.8 (3)	C9—C10—H10B	109.5
C4—C3—Br1	118.5 (3)	H10A—C10—H10B	109.5
C3—C4—C5	118.4 (3)	C9—C10—H10C	109.5
C3—C4—H4A	120.8	H10A—C10—H10C	109.5
C5—C4—H4A	120.8	H10B—C10—H10C	109.5
C6—C5—C4	121.2 (3)
C7—N1—N2—C8	−16.6 (6)	C5—C6—C7—N1	−179.9 (3)
C7—N1—N2—C9	171.9 (3)	C1—C6—C7—N1	0.7 (5)
C8—N3—N4—C9	−0.5 (4)	N4—N3—C8—N2	0.9 (4)
C6—C1—C2—C3	0.7 (5)	N4—N3—C8—S1	−177.3 (3)
C1—C2—C3—C4	−0.1 (5)	C9—N2—C8—N3	−1.0 (4)
C1—C2—C3—Br1	179.1 (3)	N1—N2—C8—N3	−173.0 (3)
C2—C3—C4—C5	−1.4 (5)	C9—N2—C8—S1	177.2 (3)
Br1—C3—C4—C5	179.4 (3)	N1—N2—C8—S1	5.1 (6)
C3—C4—C5—C6	2.3 (5)	N3—N4—C9—N2	−0.2 (4)
C4—C5—C6—C1	−1.7 (5)	N3—N4—C9—C10	180.0 (3)
C4—C5—C6—C7	179.0 (3)	C8—N2—C9—N4	0.8 (4)
C2—C1—C6—C5	0.1 (5)	N1—N2—C9—N4	174.2 (3)
C2—C1—C6—C7	179.5 (3)	C8—N2—C9—C10	−179.4 (3)
N2—N1—C7—C6	179.2 (3)	N1—N2—C9—C10	−6.0 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1N3···S1i	0.87	2.48	3.321 (4)	164
C7—H7A···S1	0.93	2.50	3.223 (4)	134

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1N3⋯S1i	0.87	2.48	3.321 (4)	164
C7—H7A⋯S1	0.93	2.50	3.223 (4)	134

Symmetry code: (i) .